US3801620A - Separation of liquid isophthalonitrile - Google Patents
Separation of liquid isophthalonitrile Download PDFInfo
- Publication number
- US3801620A US3801620A US00173810A US3801620DA US3801620A US 3801620 A US3801620 A US 3801620A US 00173810 A US00173810 A US 00173810A US 3801620D A US3801620D A US 3801620DA US 3801620 A US3801620 A US 3801620A
- Authority
- US
- United States
- Prior art keywords
- isophthalonitrile
- liquid
- ammoxidation
- xylene
- reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
Abstract
IN THE VAPOR PHASE AMMOXIDATION OF M-XYLENE TO ISOPHTHALONITRILE, THE IMPROVEMENT WHICH COMPRISES COOLING THE GASEOUS PRODUCTS FROM THE AMMOXIDATION REACTOR TO TEMPERATURE AND PRESSURE CONDITIONS WHICH WILLMAINTAIN SAID ISOPHTHALONITRILE IN THE LIQUID PHASE, SEPARATING VOLATILES FROM SAID LIQUID ISOPHTHALONITRILE, AND RECOVERING HIGHLY PURIFIED LIQUID ISOPHTHALONITRILE AS BOTTOMS.
Description
April 2, 1974 P. HosLER ETAL 3,801,620
SEPARATION OF LIQUID ISOPHTHALONITRILE Filed Aug. 2,3, 1971 INVENTORS PETER HOSLER ROBE TABAI I LlE BW 7 AGENT United States Patent() 3,801,620 SEPARATION OF LIQUID ISOPHTHALONITRIL Peter Hosler, Wallingford, and Robert A. Baillie, West Chester, Pa., assignors to Sun Research and Development Co., Philadelphia, Pa.
Filed Aug. 23, 1971, Ser. No. 173,810 Int. Cl. C07c 121/54 Us. cl. 26o-465 c z claims ABSTRACT F THE DISCLOSURE The ammonoxidation of m-xylene to isophthalonitrle s a well-known reaction described in the lierature and in numerous patents. In typical vapor phase ammoxidation procedures, the gaseous eluent from the ammoxidation reactor is coled by heat exchange, and the cooled gases quenched with water to produce an aqueous slurry of the water insoluble isophthalic acid. This product is then ltered, Washed, recovered, and often remelted for further purication by distillation (see U.S. 3,462,476, I. P. ODonnell et al., issued Aug. 19, 1969). An alternate procedure for recovery and purication of isophthalonitrile is to use an organic solvent system from which the isophthalonitrile is subsequently crystallized, lltered, washed, andotherwise purified.
An improved process for recovering isophthalonitrile from the ammoxidation of m-xylene is now provided which offers a highly ecient and economical method and avoids the ditliculties inherent in solids handling procedures. Thus, ltering and washing steps are avoid which, in turn, reduces both operational difficulties and capital investment for equipment. Furthermore, the process of the invention provides isophthalonitrile in liquid form which is a highly preferred form for further use in processing it to items of commerce; e.g. hydrolysis to isophthalic acid.
In accord with the invention, an improved process step in the vapor phase ammoxidation of m-xylene to isophthalonitrile is provided which comprises condensing thet gaseous products from the ammoxidation reactor to the liquid state, separating volatiles, and recovering isophthalonitrile at bottoms.
The process of this invention is applicable to any vapor phase ammoxidation of m-xylene and this will include those ammoxidation procedures with an without oxygen and with any of the numerous catalysts useful in such processes. Also, the vapor phase ammoxidation may be carried out in a fixed bed, moving bed, uidized bed or other type of reaction means for obtaining contact of the reactant vapors with the catalyst. Examples of typical ammoxidation procedures are set forth in U.S. 3,478,082 (Huibers, issued Nov. 11, 1969), U.S. 3,079,422 (Pasky, issued Feb. 26, 1963), and U.S. 3,501,517 (Hughes et al., issued Mar. 17, 1970).
It will also be understood that the quality of the m- Xylene reactant fed into the ammoxidation process will vary and will depend upon its source, but in general the m-xylene used Will be about 80% to about 98% pure. The impurities in the feed m-Xylene will be predominantly the ortho and para isomers of xylene, ethylbenzene, toluene, and the like. During ammoxidation, not all of the Xylenes are converted to nitrile, and conversion of only one alkyl group may occur so that the effluent contains 3,801,620 Patented Apr. 2, 1974 ice unreacted xylene, mono-nitrile (c g. toluonitrile, and benzonitrile), and the like. It is these unreacted xylenes, unwanted nitriles, water of reaction and unreacted ammonia which are eiliciently removed by the process of this invention to yield high purity isophthalonitrile.
In carrying out the process of the invention the gaseous effluent from the ammoxidation reactor will be cooled from its exiting temperature in order that the isophthalonitrile will condense to the liquid phase and this will require that the temperature of the effluent be reduced to a. temperature of about 280 F. to about 460 F., preferably about 325 to about 375 F. It will be understood that any type of heat exchange device or method may be used, preferable techniques including a water quench system, and standard heat exchangers. The cooled liquid, which is in essential equilibrium with a vapor phase comprised of the unwanted materials, is then subjected to one or more separation procedures. Preferably the liquid held at about 350 F. will be subjected to a rst separation by ashing at about 40 p.s.i.a to remove the more volatile materials such as water, ammonia, Xylene, etc., and this will be followed by a standard distillation at about 450 to 550 F. at a pressure of about 15 to 40 p.s.i.a to remove almost all of the impurities overhead. By operating in this manner, the remaining still bottoms consist of high purity (over 98%) isophthalonitrile.
In order to further describe the invention reference is now made to the following examples.
EXAMPLE l The drawing and the following description serve to examplify the process.
A xylene mixture, consisting of m-xylene, 1.6% o-xylene, 0.9% p-xylene and 2.4%ethylbenzene is charged through line 1 to an ammoxidation reactor 3 at the rate of 10,000 lb./hr. Substantially anhydrous ammonia, 15,400 lb./hr. (line 2), and the recycle stream 14 are simultaneously charged to the reactor, after preheating to 750 F. The reactor contains a catalyst of vanadia, either pure or held on an inert support, such as alumina. The reactor is operated cyclicly, so that the vandia serves alternately as an oxygen donor for the ammoxidation cycle, and then the reduced vanadia is re-oxidized in a separate cycle with oxygen-containing gas. The figure illustrates the reactor 3 to be of the fixed-bed type, where the reaction columns are alternated from ammoxidation stream to re-oxidation, on a cyclic basis. The reaction product stream 4, 28,700 lb./hr., contains 3.8 wt. percent xylenes, 1.0% benzonitrile, 3.7% toluonitrile, 44.0% phthalonitriles, .3% carbon dioxide, 34.8% water, and 12.4% ammonia. To this stream, which is at 750 F., is added through line 5 approximately 6,000 lb. of water per hour and the combined stream 6 is passed to a ash tower 7 at the resulting temperature of 350 F., 40 p.s.i.a. Liquid isophthalonitrile (IPN) is withdrawn from the bottom of the ash tower through line 8 at the rate of 12,840 lb./hr., with the following composition: 0.6 wt. percent xylenes, 0.7% benzonitrile, 3.8% toluonitriles, and 95.0% phthalonitriles. Liquid IPN in line 8 is purified in distillation column 9 to give a dinitrile product 10 with a purity of 99.9%.
As can be seen from the drawing, the overhead from ilash tower 7 is taken through line 12 to flash tower 15 held at 100 F. and 40 p.s.i.a., where ammonia and CO2 are taken overhead throughline 16. The water bottoms are then passed through line 17 to a still 18 where the hydrocarbons are split olf in the overhead 19 and combined with the hydrocarbon overhead 20 from distillation column 9. This combined stream 21 enters still 11, the overhead Xylene inline 13 being recycled and the bottoms passed through line 22 to still 12 where benzonitrile is taken overhead. The nitrile bottoms from still 12 (predominantly toluonitrile) are taken through line 14 for recycle to the ammoxidation reactor 3.
Details of these distillations are:
Temp., F.
Reflux Pressure, Column OVHD Btms. Stages ratio p.s.i.a.
"EXAMPLE 2 An ammoxidation reaction is conducted as described in Example 1, but reaction stream 6 is cooled indirectly with a heat exchanger to 360 F., 40 p.s.i.a., before passing to the flash tower. The composition of the liquid IPN from the bottom of the flash tower is: 0.7 wt. percent xylenes, 0.6% benzonitrile, 4.1% toluonitriles, and 94.5% phthalonitriles. The remainder of the purification and recycle scheme is similar to that given in Example l.
EXAMPLE 3 The invention claimed is:
1. In the vapor phase ammoxidation process for conversion of m-xylene to isophthalonitrile, the improvement which comprises cooling the gaseous products from the ammoxidation reactor by a water `quench to a temperature of about 350 F., at a pressure of about 40 p.s.i.a. in order to maintain said isophthalonitrile product as a liquid, ashing oft water, ammonia, volatile by-products, and unreacted xylene at about 350 lF. at 40 p.s.i.a., withdrawing isophthalonitrile product as bottoms, distilling off remaining impurities at about 500 F. to about 540 F., at about 40 p.s.i.a. and withdrawing highly puri- :ed liquid isophthalonitrile from the still bottom.
2. In the vapor phase ammoxidation process for conversion of m-xylene to isophthalonitrile, the improvement which comprises cooling the gaseous products from the ammoxidation reactor by a Water quench to a temperature of from about 280 F. to about 460 F., at a pressure of from about 15 to about 40 p.s.i.a. in order to maintain said isophthalonitrile product as a liquid, flashing olf water, ammonia, volatile by-products, and unreacted xylene at about 325 F. to 375 F. at 40 p.s.i.a., withdrawing isophthalonitrile product as bottoms, distilling off remaining impurities at about 450 F. to about 550 F. at about l5 to 40 p.s.i.a., and withdrawing highly purified liquid isophthalonitrile from the still bottom.
References Cited UNITED STATES PATENTS 10/ 1969 Ikeda et al. 260-465 9/ 1965 Teramoto et al. 260-465 X U.S. Cl. X.R. 260-465 H
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17381071A | 1971-08-23 | 1971-08-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3801620A true US3801620A (en) | 1974-04-02 |
Family
ID=22633593
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00173810A Expired - Lifetime US3801620A (en) | 1971-08-23 | 1971-08-23 | Separation of liquid isophthalonitrile |
Country Status (5)
Country | Link |
---|---|
US (1) | US3801620A (en) |
JP (1) | JPS4829738A (en) |
CA (1) | CA956649A (en) |
DE (1) | DE2241365C3 (en) |
GB (1) | GB1355780A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4116999A (en) * | 1977-04-28 | 1978-09-26 | The Lummus Company | Recovery of terephthalonitrile |
FR2391193A1 (en) * | 1977-05-17 | 1978-12-15 | Lummus Co | PROCESS FOR RECOVERING ISOPHTALONITRILE FROM REACTIONAL EFFLUENTS CONTAINING WATER VAPOR |
CN110590603A (en) * | 2019-10-17 | 2019-12-20 | 江苏新河农用化工有限公司 | Method for continuously rectifying and purifying m-phthalonitrile |
CN113429317A (en) * | 2021-06-22 | 2021-09-24 | 四川金象赛瑞化工股份有限公司 | Non-liquid phase production method of phthalonitrile |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2454758A1 (en) * | 1979-04-23 | 1980-11-21 | Nordh Sven | METHOD AND COMPOSITION FOR NATURALIZING CONIFERANT PLANTS |
JPS6056901A (en) * | 1983-08-11 | 1985-04-02 | Munehisa Kashiwada | Making of flowers in water |
JP4929523B2 (en) * | 2000-09-21 | 2012-05-09 | 三菱瓦斯化学株式会社 | Method for producing isophthalonitrile |
-
1971
- 1971-08-23 US US00173810A patent/US3801620A/en not_active Expired - Lifetime
-
1972
- 1972-04-07 CA CA139,166A patent/CA956649A/en not_active Expired
- 1972-06-21 JP JP7261431A patent/JPS4829738A/ja active Pending
- 1972-08-23 DE DE2241365A patent/DE2241365C3/en not_active Expired
- 1972-08-23 GB GB3920072A patent/GB1355780A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4116999A (en) * | 1977-04-28 | 1978-09-26 | The Lummus Company | Recovery of terephthalonitrile |
FR2391193A1 (en) * | 1977-05-17 | 1978-12-15 | Lummus Co | PROCESS FOR RECOVERING ISOPHTALONITRILE FROM REACTIONAL EFFLUENTS CONTAINING WATER VAPOR |
CN110590603A (en) * | 2019-10-17 | 2019-12-20 | 江苏新河农用化工有限公司 | Method for continuously rectifying and purifying m-phthalonitrile |
CN110590603B (en) * | 2019-10-17 | 2021-12-07 | 江苏新河农用化工有限公司 | Method for continuously rectifying and purifying m-phthalonitrile |
CN113429317A (en) * | 2021-06-22 | 2021-09-24 | 四川金象赛瑞化工股份有限公司 | Non-liquid phase production method of phthalonitrile |
Also Published As
Publication number | Publication date |
---|---|
JPS4829738A (en) | 1973-04-19 |
DE2241365A1 (en) | 1973-03-08 |
DE2241365C3 (en) | 1981-01-15 |
GB1355780A (en) | 1974-06-05 |
DE2241365B2 (en) | 1980-05-08 |
CA956649A (en) | 1974-10-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7071348B2 (en) | Process for the purification of olefinically unsaturated nitriles | |
EP0117146B1 (en) | Conversion of propane to acrylic acid | |
US3936360A (en) | Process for distillation and recovery of olefinic nitriles | |
JP4664507B2 (en) | An improved method for the recovery of acrylonitrile and methacrylonitrile. | |
US2526676A (en) | Process for producing acrylonitrile | |
US3174262A (en) | Chemical process and apparatus for recovery of ethylene oxide | |
US4269667A (en) | Acrylonitrile purification by extractive distillation | |
US3801620A (en) | Separation of liquid isophthalonitrile | |
US4434029A (en) | Process for producing unsaturated nitrile | |
US3404177A (en) | Producing and recovering vinyl acetate from a gaseous mixture by fractional distillation | |
US4172209A (en) | Process for producing dicarboxylic acids by the oxidation of xylene | |
US6296739B1 (en) | Operation of heads column | |
US3109864A (en) | Oxidation of hydrocarbons | |
US3776949A (en) | Production of aromatic polycarboxylic acids | |
US3328266A (en) | Modiano etal separation of acrylonitrile by extractive distillation with water | |
US5629444A (en) | Acrylonitrile recovery process | |
US3051630A (en) | Purification of acrylonitrile | |
US3758572A (en) | Process for recovering urea from pyrolysis systems | |
US3201918A (en) | Process for separating acrylonitrile and ammonia from gaseous mixtures | |
KR100725683B1 (en) | Method of purifying isophthalonitrile | |
US3682782A (en) | Reduced pressure distillation process for recovering aniline from phenolaniline mixtures | |
US3294856A (en) | Process for preparation and purification of styrene | |
US3636067A (en) | Purification of acrylonitrile by absorption plural distillation andrecycle of bottoms stream to the absorber | |
US3544274A (en) | Halogen production | |
US3120568A (en) | Recovery of allyl chloride |